The Best Musical Guests on 'The Simpsons'

Nicole Wilder/FOX
Katy Perry onĀ The Simpsons.

On Sunday night (Sept. 25) The Simpsons entered its perfectly cromulent 28th season.  Over the course of their nearly 600 episodes, the Simpson family have done just about everything and met just about everyone. (After all, “Simpsons did it!”)

One of the best things about The Simpsons has always been their memorable musical moments, whether they are taking in a Broadway musical (“I love you, Dr. Zaius!”), or breaking into a show tune of their own (“Monoraiiiiiil!”).

But, it’s not just the Simpson clan and company with the pipes to sing “We Put the Spring in Springfield.” Since their debut in 1989, The Simpsons have been serenaded by everyone from The Dixie Chicks to Aerosmith to James Brown and crossed paths with the likes of Katy Perry, ‘NSYNC, and Dolly Parton, among many others.

In other words, musical guests are as essential to The Simpsons as the nuclear power plant and donuts. Mmm, donuts. In celebration of Season 28, we’re looking back at the best musical guests of the series thus far.

Johnny Cash in “El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)"

This is, arguably, one of the best Simpsons episodes of all-time and that’s thanks largely in part to the voice work of the one and only Johnny Cash. After ingesting some Guatemalan insanity peppers, Homer goes on a journey of the mind and soul, where he encounters his wise spirit guide known as “Space Coyote,” voiced beautifully by Cash.

 

U2 in “Trash of the Titans”

U2 brought their PopMart tour to Springfield at the same time that Homer was running his campaign for Sanitation Commissioner, a cause near and dear to Bono’s heart. (“He’s talking about waste management, and that affects the whole damn planet!”) Not only did we get to see U2 perform “Pride (In the Name of Love)” on The Simpsons, but we learned that the best way to sneak backstage into a U2 concert is to tell security you’re their potato man.

 

Michael Jackson in “Stark Raving Dad”

When Homer winds up in a mental institution he meets Michael Jackson. Or, at least, a guy that sounds a hell of a lot like him. (The character, Leon Kompowsky was, indeed, actually voiced by the King of Pop himself.) In the classic episode, Michael—d’oh!—Leon helps Bart pen a tune to Lisa, called “Happy Birthday, Lisa” and it’s arguably the best Michael Jackson song related to The Simpsons. (Sorry, “Do the Bartman.”)

Sir Paul McCartney in “Lisa the Vegetarian”

Sir Paul, accompanied by his late wife Linda McCartney, didn’t perform anything during their visit to The Simpsons, but for a cameo this great, they really didn’t need to. (Besides, Apu’s rendition of “Sgt. Pepper’s Lonely Hearts Club Band” sure was…something.) Lisa meets Paul and Linda gardening on the roof of the Kwik-E-Mart to discuss vegetarianism and animal rights, and with all due respect to Ringo and George, it was the best Beatles. Cameo. Ever.

 

The Entire Hullabalooza Lineup in “Homerpalooza”

Billy Corgan, Smashing Pumpkins.
Homer Simpson, smiling politely.

That exchange in and of itself made the Smashing Pumpkins one of the best musical guests ever, but how could we leave out an annoyed Peter Frampton and his riffs with Sonic Youth and Cypress Hill?

 

Sting in “Radio Bart”

“Sending Our Love Down the Well” became the “We Are the World” of The Simpsons universe when Bart posed as Timmy O’Toole, a fictitious boy trapped in a well. Celebrities joined together to make the charity track, lead by none other than Krusty the Klown’s good friend Sting.

 

Bette Midler in “Krusty Gets Kancelled”

This episode featured wall-to-wall celebrity guests, including Johnny Carson, Luke Perry, and the Red Hot Chili Peppers, who all appear on Krusty’s comeback special. But it’s Bette Midler who takes the cake for her hilarious method of cleaning up the streets of Springfield, as well as her emotional “Wind Beneath My Wings” duet with Krusty.

 

James Taylor in “Homer in Space”

When Homer causes a dangerous situation in outer space thanks to some ruffled potato chips and a broken ant farm, the only person who could truly save the day (besides the inanimate carbon rod) was former President/music superstar James Taylor.

 

Paul Anka in “Treeehouse of Horror VI”

Leave it to The Simpsons and Paul Anka to make a song about ignoring rampaging billboards and advertisements that have come to life that’s not only funny and catchy, but also incredibly poignant.

 

Tito Puente in “Who Shot Mr. Burns?”

The legendary mambo musician played a pivotal role in one of the most iconic television cliffhangers of all-time, as both Lisa’s new jazz instructor at Springfield Elementary and, eventually, a suspect in the shooting of Mr. Burns. He also penned a pretty snazzy song about the whole ordeal.

Robert Goulet in “$pringfield”

Marge had a gambling problem when Mr. Burns casino opened in Springfield, but the real star of this episode was crooner Robert Goulet, who got conned into singing off-beat Christmas songs at Bart’s treehouse casino.

 

Weird Al Yankovic in “Three Gays of the Condo”

Sure, it was no “Another One Bites the Crust,” but Weird Al’s ode to Homer and Marge, “Love Goes On,” was enough to reunite the temporarily estranged pair. That’s the power of Weird Al.

 

Spinal Tap in “The Otto Show”

The Simpsons and This is Spinal Tap! are two of the most influential pieces of musical comedy in pop culture history, so it made sense that when they came together they’d be in perfect harmony. That’s because nobody rocks like… Springfield.

 

Phish in “Weekend at Burnsies”

Just like they would during any of their shows, Phish demanded to see the medical marijuana prescriptions of the Springfield concertgoers.

 

The Rock ‘N Roll Fantasy Camp gang in “How I Spent My Strummer Vacation”

Mick Jagger, Keith Richards, Lenny Kravitz, Tom Petty, Brian Setzer, and Elvis “My Image!” Costello gave Homer and friends a crash course in what it takes to be a rock star, but you know, “without the lawsuits and STDs.”